1-[Methylated piperidino(and pyrrolidin-1-yl)]-3-(substituted phenoxy)-2propanols

• US 3,954,776 A
• Filed: 08/23/1974
• Issued: 05/04/1976
• Est. Priority Date: 08/23/1973
• Status: Expired due to Term

• Current Assignee: Yoshitomi Pharmaceutical Industries, Ltd. (UBE Corporation)
• Original Assignee: Yoshitomi Pharmaceutical Industries, Ltd. (UBE Corporation)
• Inventors: Ogawa, Kiyoshi, Muro, Tomio, Chihara, Yasuaki, Fukuzawa, Sogo, Nakao, Tohru
• Primary Examiner(s): Winters, Sherman D.
• Application Number:
  US05/499,948
• Time in Patent Office: 620 Days
• Field of Search: 260/293.67, 260/293.68, 260/293.69, 260/296 R, 260/326.5 D, 260/326.5 SM
• US Class Current: 546/194
• CPC Class Codes: C07D 295/088 to an acyclic saturated chain

Abstract

1-[Methylated piperidino (and pyrrolidin-1-yl)]-3-(substituted phenoxy)-2-propanols of the formula: ##SPC1##

Wherein R is a 2-thienylmethyl group, a 2-pyridylmethyl group, a 2-pyridyl group, a tetrahydrofurfuryloxy group, a furfuryloxy group, a 2-thienylmethoxy group, a 2-pyridyloxy group or a group of the formula R⁵ --X--A--O-- wherein R⁵ is a lower alkyl group, X is --O--, --S-- or --SO₂ --, and A is a lower alkylene group or a --CH₂ --C≡C--CH₂ -- group, R¹ is a hydrogen atom, a lower alkyl group or a halogen atom, R², R³ and R⁴ are each a hydrogen atom or a methyl group, and n is zero or 1, and pharmaceutically acceptable acid addition and quarternary ammonium salts thereof are disclosed. They exhibit antiarrhythmic action, local anaesthetic action, analgesic action and gastric juice secretion inhibiting action.

Claims

1. A compound of the formula:

##SPC7##

wherein R is a 2-thienylmethyl group, a 2-pyridylmethyl group, a 2-pyridyl group, a tetrahydrofurfuryloxy group, a furfuryloxy group or a 2-pyridyloxy group;

R¹ is a hydrogen atom, a lower alkyl group or a halogen atom;

R², R³ and R ⁴ are each a hydrogen atom or a methyl group; and

n is zero or 1; and

pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.

2. The compound of claim 1 wherein R is a 2-thienylmethyl group and R¹ is a hydrogen atom.

3. The compound of claim 1 wherein R is a 2-pyridylmethyl group and R¹ is a hydrogen atom.

4. The compound of claim 1 wherein R is a 2-pyridyl group and R¹ is a hydrogen atom.

5. The compound of claim 1 wherein R is a tetrahydrofurfuryloxy group and R¹ is a hydrogen atom.

6. The compound of claim 1 wherein R is a furfuryloxy group and R¹ is a hydrogen atom.

7. The compound of claim 1 wherein R is a 2-pyridyloxy group and R¹ is a hydrogen atom.

8. The compound of claim 1;

1-(2,2,6,6-tetramethylpiperidino)-3-[2-(tetrahydrofurfuryloxy)phenoxy]-2-propanol.

9. The compound of claim 1:

1-(2,2,5,5-tetramethylpyrrolidin-1-yl)-3-[2-(furfuryloxy)phenoxy]-2-propanol

10. The compound of claim 1:

1-(2,2,6,6-tetramethylpiperidino)-3-[2-(2-pyridylmethyl)phenoxy]-2-propano

11. The compound of claim 1:

1-(2,2,6,6-tetramethylpiperidino)-3-[2-(2-pyridyloxy)phenoxy]-2-propanol

12. The compound of claim 1:

1-(2,2,6,6-tetramethylpiperidino)-3-[2-(furfuryloxy)phenoxy]-2-propanol

13. The compound of claim 1:

1-(2,6-dimethylpiperidino)-3-[2-(2-thienylmethyl)phenoxy]-2-propanol

14. The compound of claim 1:

1-(2,2,6,6-tetramethylpiperidino)-3-[2-(2-thienylmethyl)phenoxy]-2-propanol

15. The compound of claim 1:

1-(2-methylpiperidino)-3-[2-(2-thienylmethyl)phenoxy]-2-propanol

16. The compound of claim 1;

1-(2-methylpiperidino)-3-[4-(2-thienylmethyl)phenoxy]-2-propanol